Ellie Jackson: From ‘ditzy’ apprentice to ‘tenacious’ broker MD in five years – How thoughtful succession planning is unlocking new growth opportunities at Robert Gerrard

The Covid-19 pandemic in 2020 massively skewed Ellie Jackson’s well laid career plans.

After completing her advanced level qualifications at Essex’s Chigwell School, she started at the University of the Arts London in 2019, specifically joining its London College of Fashion to study makeup and prosthetics for television and film.

However, the onset of the pandemic soon after her university tenure began severely restricted Jackson’s job options where her first choice “industry was shut down overnight”. As a result, Jackson leaned into her old school motto – “find a way or make a way” – to quiz family and friends about viable career opportunities.

A friend from primary school put Jackson in touch with her mother – Carla Preston, formerly managing director at Chingford-based commercial and high net worth broker Robert Gerrard – who was looking for an apprentice to join her family founded firm.

Just five years on from this pivotal conversation – and after completing two apprenticeships, as well as the Chartered Insurance Institute’s certificate and diploma in insurance – 28-year-old Jackson was named by Preston as her successor upon retirement following a 40-year tenure, effective from 1 August 2026.

As Robert Gerrard’s new managing director, Jackson is now the custodian of the 50-year-old Jensten Group-owned broker, which has 21 staff, including two apprentices, handles £11m gross written premium and helps insure around 1,000 UK businesses within its lift and escalator sweet spot sector.

“It’s quite surreal when you say it out loud, but a lot has been packed into that five-year journey,” Jackson tells Insurance Times in her first exclusive interview following her promotion.

“I want to be the best managing director possible and I will do anything to work towards that.

“It’s a huge milestone for me. I don’t take it lightly, but it’s not the end of my journey. I’m really excited about the challenges that are going to come and trying to just take everything in my stride. If I don’t know something, I’ll learn it.”

Succession planning in action

Jackson’s trajectory at Robert Gerrard reads very much like a traditional career ladder climb, with her two-year apprenticeship followed by positions such as account executive, senior account executive, team leader and sales development manager, before hitting the top job last month.

During this time, and in particular over the last three years, Jackson says her job “role became broader because I was increasingly involved in conversations around growth, strategy, people and [the] overall direction of the business”.

With this widening remit, Jackson was able to showcase and implement her own initiatives and leadership. This included, for example, launching a customer-centric cyber campaign last summer that resulted in cyber insurance take-up from the broker’s clients improving from 5% to 15% in the subsequent 12 months, as well as introducing The Pipeline Club last year to mentor junior colleagues and provide support around lead generation and career progression.

However, Jackson really dared to let her ambitions of becoming managing director take a more solid form around 18 months ago, after intermediary organisation Jensten Group bought Robert Gerrard in August 2024 to join its schemes and affinities portfolio.

She tells Insurance Times: “Succession is very much a part of that plan when you sell your business. Until then, becoming managing director was certainly an ambition. But there’s a big difference between privately aspiring to something and then people actually believing you can do that.

“That shift is quite difficult to manage because you’re sitting there waiting for something to happen or something to be told to you. But I kept asking the question ‘am I on track? Am I doing what I need to do in my role now to show that I can be ready for the next step?’”

Preston did determine that Jackson was ready for the next career step – however the promotion did not happen overnight.

Jackson built on her 25-year childhood relationship with Preston – as the mother of her friend – to learn the leadership ropes firsthand, with Jensten Group giving the nod of approval too by accepting Jackson onto its Leading Lights leadership apprenticeship two years ago and providing mentoring from members of its executive committee.

This support to develop Jackson into the “visible, supportive and demanding” leader she describes herself as being today is “a brilliant example about what succession planning should be”, she adds.

“Appointing a 28-year-old who joined the industry five years ago isn’t necessarily the obvious or safest choice on paper,” Jackson acknowledges.

“They could have easily decided to bring somebody in with 20-years’ management experience – but instead, they looked at what I’d achieved, [my] relationships within the business, my understanding of the business and they believed what I could become.

“I’m not there yet, [but] they gave me that opportunity and I’m just very grateful for that. It’s a brilliant example about what succession planning should be. It’s not just identifying someone who can do the job today, but where will that person be in two, three years’ time? You can give people experience, but recognising that [future] talent is something that I think people really struggle with.

“Preston really invested in me and Jensten Group took the leap of faith – I very much feel like I have to repay them at the moment.”

Although following in Preston’s footsteps, Jackson is keen to emphasise that she will not be filling her former mentor’s shoes exactly – more putting her “own stilettos on” as she crafts her own era of leadership at Robert Gerrard, focused on tenacity, nurturing talent and being client focused.

Jackson continues: “Succession works well when you don’t come in and pretend to be someone else.

“I’m not Preston. We lead very differently and what I want to do is protect what she’s built because she worked so hard to build it. But I want to lead in my own way and be respected for that.

“I don’t think putting my mark on the business means changing everything. I’d rather [that] over time, people see what we achieve and my results will be my legacy, just like Preston’s [are].

“I’m particularly passionate about creating opportunities for young people because I experienced what that was like. I’d love to emulate that and I’d love apprentices coming into the business thinking ‘why can’t that be me?’ Because I felt like that with Preston.

“But I’m very different and that is why I’ve been successful within the five years.”

The next five years

But now that Jackson has made it into pole position at Robert Gerrard, what does she plan to do?

“I’m not just going to come in and change things for the sake of it when they don’t need changing,” she says. “But I want the curiosity of what an external candidate would bring, looking at the business with a fresh set of eyes, some fresh energy.

“I’m not coming in and ripping the building apart. It’s very much finding my feet as a leader, making sure we deliver on the numbers, making sure there’s some continuity and making sure the team are ok because it’s a big change for them.”

She initially prepared for her promotion by putting together “the first business plan I ever wrote” a little over eight months ago, ditching a document strewn with spreadsheets in favour of an “unconventional” explainer “all about doing the simple things well, pulling the levers that we can control and delivering on those numbers”.

For Jackson, “a big part” of her five-year strategy is around nurturing “organic growth” – which is why she has devised a number of “bigger projects” for the broker to action over the next two years.

For example, she plans to build on Robert Gerrard launching its lift and escalator scheme – backed by insurer Chubb – into the Irish insurance market from January 2025 by introducing it across the Channel too, broadening its international scope.

With this ambition in mind, Jackson instigated and conducted market research last year in both Germany and Italy by attending relevant trade shows. This confirmed the scale of the available opportunity, as well as Jackson’s intuition on Robert Gerrard’s direction of travel.

“In Germany, I was there for 36 hours. I saw 22 clients and created 14 opportunities,” she notes. Jackson visited the equivalent Italian trade show a month later, staying for just 24 hours to speak with sector focused insurers and lift companies.

With these geographies now set in Robert Gerrard’s crosshairs, Jackson hopes to pull the trigger on launching the broker’s lift and escalator scheme in these jurisdictions in 2027 – or 2028 at the very latest. The business would not look to set up local offices abroad, but instead service the scheme from its UK headquarters – supported by a planned boost in the firm’s 21-strong headcount.

Jackson feels that taking Robert Gerrard’s lift scheme into Europe is “the next step” if the broker wants to continue growth and sector leadership in terms of insuring this niche industry as new opportunities in the UK are reducing as the scheme’s customer count increases.

She explains: “We’ve serviced this sector for 50 years and we’ve got to a point capacity wise within the UK market [where] we service quite a large proportion of the lift and escalator market – probably around 50%.

“You’re only going to grow so much in the UK and a lot of the larger lift companies have either an international parent company, or are based outside the UK. So, if you want to go into that larger corporate world, [expanding internationally] is naturally the next step.

“Having our UK clients interlinked with [European entities] already gives us that introduction, so naturally, it just feels like [this] should be the next step.”

Jackson is not putting all her eggs in the international basket, however.

Once her plans for Germany and Italy have come to fruition, she wants to revert the business’ focus back to home turf to explore “adjacent scheme” opportunities to run alongside the successful lift and escalator proposition.

“Whether that’s a new scheme or additional products to what we’re already doing, that is really the next piece of strategy that we’re working on,” Jackson confirms.

This involves “looking at who the lift industry already works with”, she adds, such as “plant suppliers” or “metal manufacturers”, as well as exploring “another scheme that runs at low frequency but high severity”.

Jackson continues: “It’s finding that next niche. We want to find that gap in the market where clients actually need us.”

Being part of the highly acquisitive Jensten Group also puts opportunities on the table in terms of acquisitive growth. Although Jackson says she is “definitely open” to buying businesses, the more likely route she envisions is around purchasing a set team, perhaps one centred around a new scheme. She hinted that this play is already being discussed at a group level.

True colours of leadership

Standing between a wall adorned with her insurance qualification certificates and a leaky air conditioning unit, decked out in a cream and black polka dot suit and trainers, Jackson is a revitalising breath of fresh air for the UK’s broking scene, determined to deliver professionally while still being herself.

“Five years ago, I was quite ditzy. I cared more about what I looked like than anything else. I didn’t know what insurance was or a premium – and now I’m the MD,” she says.

“For people around me, it’s probably quite surreal, but they know what I’ve achieved and they’ve celebrated everything along the way with me. I have support around me and they’re open to change and adapting.

“I’m not the same person. I’m not the makeup artist who left school. I want to prove that you can be a serious business leader, but you don’t have to typically look like your corporate managing director.

“I’m doing things slightly differently, but I just feel like I should keep my personality while doing the role and, hopefully, there’s a little bit of Essex in every boardroom.”